We need to monitor an employee’s sent and received emails on the company domain account due to recurring Customer Service complaints.

We have previously notified all employees in writing that no personal business should be conducted on the company email addresses and if there is such need, set up their own free web email with Yahoo!, Google, etc.

Anyway, is there a way to receive copies of everything this Dreamhost account sends and receives? I realize that i can simply add that account to my MS Outlook and set it to not delete emails off server and leave marked as “unread”. But, this won’t deliver copies of sent emails.

If you let Google Apps handle email on your domain, something Dreamhost makes easy, then you can download sent emails since Gmail’s POP includes sent emails too. Unfortunately Gmail just lowered the number of users on a free Google Apps account from 50 to 10, so you’ll have to pay if you need more than 10 email addresses.

I don’t believe that you can do that reliably with Google Apps - although you can download sent emails from a user’s account via IMAP, you can’t do so from a single administrative login (i.e, you need their password to do so), and they can manually delete messages from their sent box before you see them.

For this scenario I’d consider running a mail server internally just as a proxy. Configure clients to use DH for POP3 but the internal server for SMTP. I haven’t thought this through, it’s just an idea. You could then either send mail outbound direct from your server (and deal with various disparities and trust relationship issues) or (my choice) try to relay your SMTP through the more trusted DH servers so that everyone ultimately exchanges email with DH and no one knows here is another server in between unless they analyze headers. The point here is that by using an internal SMTP server you can then capture all outbound traffic. Setup POP3 to do the same if desired. There are a number of FOSS mail servers on the market, and you might be able to use the free server that comes with Windows if that will suit your needs. HTH